DE1117241B - Process for the production of water-insoluble azo dyes - Google Patents

Description

Process for the preparation of water-insoluble azo dyes It has been found that valuable, water-insoluble azo dyes are obtained if the diazonium compounds are obtained from m-aminoazo compounds of the general formula in which the benzene nuclei a and b can be substituted by halogen atoms, alkyl, alkoxy or nitro groups, with arylamides of aromatic or heterocyclic o-oxycarboxylic acids or of acyl acetic acids which are free of water-solubilizing groups, in substance, on the fiber or on another Substrate couples.

With the dyes you get on fibers made of aromatic polyesters, in particular polyethylene terephthalates, valuable dyeings that are distinguished by good Distinguish authenticity properties. The dyes can also be applied to others synthetic fibers such as acetyl cellulose, triacetyl cellulose or polyamide fibers, or on vegetable fibers, including those made from regenerated cellulose, as well as on animal fibers such as wool or silk, and likewise valuable colorations are obtained.

The dyes can also be produced in bulk or on a substrate or for coloring high molecular weight plastic masses or for preparation used by colored lacquers. You can also use it to make colored felts introduced in bulk from cellulose esters or ethers or in the pigment printing process can be applied to textiles.

The diazotization of the m-aminoazo compounds and the coupling of the so available diazoazo compounds with the aryl amides of aromatic or heterocyclic o-Oxycarboxylic acids or acyl acetic acids are carried out in a known manner.

As azo components, for example, arylamides of 2-oxynaphthalene-3-carboxylic acid, the 6-substituted 2-oxynaphthalene-3-carboxylic acid, the 5,6,7,8-tetrahydro-2-oxynaphthalene-3-carboxylic acid, of 2-oxyanthracene-3-carboxylic acid, of 2-oxycarbazole-3-carboxylic acid, of 3-oxydiphenylene oxide-2-carboxylic acid, acetoacetic acid, benzoylacetic acid or terephthaloylbisacetic acid use Find.

The preparation of those used as diazo components in the literature m-aminoazo compounds, some of which have not yet been described, can be prepared by known processes take place, for example by coupling diazotized 3-amino-1-acetylaminobenzenes with oxy compounds of the benzene series, etherification of the oxy groups and splitting off of the Acetyl group.

Compared to the disazo dye known from German patent specification 609 334 from diazotized 2-amino-4-methyl-2 ', 4'-dichloro-1,1'-azobenzene and 1- (2', 3'-oxynaphthoylamino) -2-methyl-4-chlorobenzene the disazo dyes of similar composition obtainable according to the process stand out due to a much better light and sublimation fastness of the polyethylene terephthalate dyeings the end.

Example 1 Cotton fabric is made on the padder with the following solution padded and dried: 14 g of 1- (2 ', 3'-oxynaphthoylamino) -2,4-dimethoxy-5-chlorobenzene are mixed with 20 cc of a wetting agent of the oil sulfonate type and 14 cc of sodium hydroxide solution of 38 ° B6 made into a paste, heated for 15 minutes and with boiling water, the 5 ccm one Contains wetting agent of the oil sulfonate type and 2 cc sodium hydroxide solution at 38 ° B6 1 1 set. The dried fabric is developed on the padder with a solution, 13 g of 3-amino-2-methyl-4'-methoxy-1,1'-azobenzene (F.114 to 115 ° C) in the form of a diazonium compound prepared in the usual way, 1 g one Product of action of about 20 moles of ethylene oxide to 1 mole Contains octodecyl alcohol and 60 g disodium phosphate.

After about 30 seconds of air movement, the clutch is activated by a Completed hot water passage. Then it is rinsed, 15 minutes at 95 ° C with 1 g of an action product of about 10 moles of ethylene oxide to 1 mole of isododecylphenol and 3 g of soda per liter of water soaped, rinsed and dried.

A yellowish red with good fastness properties is obtained.

Example 2 250 g of polyethylene glycol terephthalate tops are treated in a closed apparatus for 90 minutes at 120 ° C. in the following bath: 2.93 g of 1- (2 ', 3'-oxynaphthoylamino) -2-methoxybenzene and 1.42 g of 3-amino -4,4'-dimethoxy-1,1'-azobenzene (F. 159 to 160'C) get hot in a mixture of 15 ccm of diacetone alcohol, 5 ccm of a wetting agent of the oil sulfonate type and 0.95 ccm of 38 'caustic soda B6 dissolved and stirred in water at 90 ° C. which contains 1 cc of diethyl tartrate.

The 2.5 g of alkylphenyl polyglycolsulfuric acid ester is then added for 5 minutes at 80 ° C. in water and then rinsed in cold water for 5 minutes. Then with 12.5 g of sodium nitrite and 25 g of sulfuric acid (96 ° / Qig) in 51 water are diazotized by adding the dyed material is heated to 85 ° C and treated for 1/2 hour at 80 to 85 ° C.

Then it is rinsed hot and cold, with 20 ccm of sodium hydroxide solution 38'B6, 10 g of sodium dithionite and 2.5 g of alkylphenyl polyglycol sulfuric acid ester in 51 water aftertreated for 15 minutes at 80'C, rinsed hot and cold and dried.

A bluish red with good fastness properties is obtained.

Example 3 175 g of polyethylene glycol terephthalate silk are treated in the apparatus for 90 minutes at 95 ° C. in the following bath: 2.93 g of 1- (2 ', 3'-oxynaphthoylamino) -2-methoxybenzene and 1.25 g of 3-amino-4'Methoxy-1,1'-azobenzene (m.p. 80 to 81'C) are at 80'C in a mixture of 8.4 cc of tetrahydronaphthalene, 4.4 cc of diglycol, 1.7 cc of butyl alcohol, 5.4 g of a Dispersing agent of the alkylarylsulfonate type and 0.95 g sodium hydroxide solution of 38 'Be dissolved and stirred into 3.51 of water at 90'C , which contains 1 ccm of diethyl tartrate. Contains 5 g of an alkylphenyl polyglycol sulfuric acid ester, and then rinsed for 5 minutes in 3.5 liters of cold water.

Then with 8.8 g of sodium nitrite and 17.5 g of sulfuric acid 96% diazotized in 3.51 water by adding the material to be dyed 85'C heated and treated 1/2 hour at 80 to 85'C. Then in the example 2 described manner rinsed, treated, rinsed and dried.

A yellowish scarlet with good fastness properties is obtained.

Example 4 100 g acetate silk are 90 minutes at 75 ° C in the following Treated bath, after 20 minutes 10 g of table salt, dissolved in water, added are: 1.5 g of 1- (2 ', 3'-oxynaphthoylamino) -2-methyl-4-methoxybenzene and 1.2 g of 3-amino-2'-methyl-4'-methoxy-1,1'-azobenzene (F. 75 to 76'C) are in a mixture of 4.5 ccm diglycol, 4.5 ccm monoethanolamine, Dissolve 0.5 ccm of sodium hydroxide solution at 38 ° B6 and 2 ccm of water in the heat and put in a bath stirred in from 75'C, 3 ccm ammonia solution (25%) and 9 g of one in 3 1 of water Condensation product from high molecular weight fatty acids and protein degradation products contains.

Then it is rinsed cold and 15 minutes with 3 g of sodium nitrite and 15 ccm hydrochloric acid of 20 ° B6 in 3 liters of cold water. Then 15 minutes at 80 ° C with 6 g of sodium acetate. 6 g of an action product of about 20 moles of ethylene oxide to 1 mol of octodecyl alcohol and 3 g of the sodium salt of nitrilotriacetic acid in 31 water post-treated, rinsed and dried.

A red-orange with good fastness properties is obtained.

Polyamide fibers can also be dyed in the same way, whereby however, it is advisable to use twice the amount of sodium nitrite in the diazotization and hydrochloric acid.

Example 5 100 g of triacetate silk are used for 2 hours at 90.degree. C. in the following Bath treats: 2.1 g of 1- (2 ', 3'-oxynaphthoylamino) -2-methoxybenzene and 1.2 g of 3-amino-3'-chloro-4'-methoxy-1,1'-azobenzene (F. 94 to 95'C) are in a mixture of 24 cc diacetone alcohol and 1 cc sodium hydroxide solution of 38'B6 dissolved in the heat and stirred into 31 water at 90'C. After 30 and 1 cc of diethyl tartrate are added to the bath for 60 minutes.

Then it is rinsed and at 25 to 30'C with 6 g of sodium nitrite and 7.5 ccm hydrochloric acid of 20'B6 in 3 l of water is diazotized by, after the introduction the dyed material is heated to 80 ° C. and treated for 1/2 hour at this temperature.

It is then rinsed, 15 minutes at 80 to 85 ° C with 6 g of sodium carbonate, 1.5 g of sodium dithionite and 3 g of a condensation product from an aminoalkylsulfonic acid and a higher molecular weight fatty acid in 31 water, rinsed, again 15 minutes at 90 ° C. with 6 g of sodium carbonate and 3 g of a condensation product from an aminoalkylsulfonic acid and a higher molecular weight fatty acid in 31 water post-treated, rinsed and dried.

A yellowish scarlet with good fastness properties is obtained.

Example 6 1 kg of polyethylene glycol terephthalate sliver is 90 minutes treated at 95 to 100'C in the following bath: 21.1 g of 4,4'-bisacetoacetylamino-3,3'-dimethoxydiphenyl, 6.9 g of 3-amino-4'-methoxy-1,1'-azobenzene and 2.22 g of sodium hydroxide are heated in a mixture of 45 cc tetrahydronaphthalene, 24 cc diglycol, 9 cc butyl alcohol and 29 g of a dispersant of the alkylarylsulfonate type dissolved and in 201 Entered water at 90'C, the 6.5 g of tartaric acid diethyl ester are added.

It is then rinsed with 40 g of sodium nitrite and 100 g of sulfuric acid (96%) diazotized in 201 water, by looking after bringing in the dyed material is heated to 85 ° C and treated at 80 to 85 ° C for 30 minutes.

It is then rinsed for 15 minutes at 80 ° C. with 80 cc of sodium hydroxide solution of 38'B6, 40 g of sodium dithionite and 20 g of a nonionic detergent in 201 Post-treated with water, rinsed and dried.

A strong yellow with good fastness properties is obtained.

In the above example, 4,4'-bisacetoacetylamino-3,3'-dimethoxydiphenyl is used in place of 21.1 g 29.4 g of 1-acetoacetylamino-2,5-dimethoxy-4-chlorobenzene are obtained as opaque Yellow with similarly good fastness properties.

Example 7 1 kg of polyethylene glycol terephthalate sliver is treated for 90 minutes at 95 to 100 ° C. in the following bath: 17.2 g of 1- (2 ', 3'-oxynaphthoylamino) -2-methyl-4-methoxybenzene, 8 g of 3- Amino-4,4'-dimethoxy-1,1'-azobenzene and 2.2 g of sodium hydroxide are dissolved hot in a mixture of 45 cc of tetrahydronaphthalene, 24 cc of diglycol, 9 cc of butyl alcohol and 29 g of a dispersant of the alkylarylsulfonate type and in 201 Stir in water at 90 ° C., to which 6.5 g of diethyl tartrate are added.

Then, as described in Example 1, rinsing, diazotization and treated, rinsed again and dried.

A bluish red dyeing with good fastness properties is obtained.

Example 8 1 kg of polyethylene glycol terephthalate sliver is 90 minutes treated at 95 to 100 ° C in the following bath: 18.4 g of 1- (2'-oxycarbazole-3'-carboylamino) -2-methoxybenzene, 7.3 g of 3-amino-4-methyl-4'-methoxy-1,1'-azobenzene (mp 151 to 152 ° C) and 2.2 g of sodium hydroxide get hot in a mixture of 45 ccm tetrahydronaphthalene, 24 ccm diglycol, 9 cc of butyl alcohol and 29 g of a dispersant of the alkylarylsulfonate type dissolved and stirred into water at 90 ° C., to which 6.5 g of diethyl tartrate are added admits.

Then, as described in Example 1, rinsing, diazotization and treated, rinsed again; and dried.

A strong leather brown with good fastness properties is obtained.

Example 9 100 g of wool yarn are used for 1 hour at 55 to 60 ° C in the following Bath, to which, after 30 minutes, 60 g of table salt, dissolved in 300 ccm of water, added: 3 g of 1- (2 ', 3'-oxynaphthoylamino) -2-methyl-4-chlorobenzene in the form of the sodium salt are dissolved in 6 cc of denatured alcohol, 7.5 cc of water at 40 ° C and 3.6 cc of formaldehyde solution (33%) dissolved and stirred in a bath containing 6 g of a condensation product contains higher molecular weight fatty acids and protein breakdown products as well as 6 g sodium carbonate. Then make up to 31 with water. Then 5 minutes with 40g of table salt and 3 g of sodium carbonate in liter of water rinsed and 1/2 hour in the following Bath developed: 4.35 g of 3-amino-6,4'-dimethoxy-1,1'-azobenzene are 6.9 cc Hydrochloric acid at 20 ° B6 and 1.4 g of sodium nitrite, dissolved in 7 cem of water, diazotized and stirred in a bath containing 3 g of an action product of about 20 moles of ethylene oxide to 1 mole of a fatty alcohol. Then with mono- and disodium phosphate adjusted to pA 4 and made up to 3 l with water.

This is followed by 15 minutes at 60 ° C with 5 g of soap and 3 cem concentrated ammonia solution in liter of water and then 15 minutes at 85 ° C with 1 g of a condensation product of an aminoalkylsulfonic acid and a higher molecular weight Fatty acid and 0.5 cc of acetic acid (50%) per liter of water are aftertreated, rinsed and dried.

A brownish garnet is obtained. Example 10 100 g of natural silk can be used pre-wetted and treated for 50 minutes at 20 to 25 ° C in the following bath, the after 30 minutes, 60 g of common salt, dissolved in 300 cc of water, are added: 7.5 g of 1- (2 ', 3'-oxynaphthoylamino) -2-methyl-4-chlorobenzene are in 12 cc of denatured alcohol, 3.75 cc of sodium hydroxide solution at 38 ° B6, 15 cc of water of 40 ° C and 3.6 ccm formaldehyde solution (33%) dissolved and stirred in a bath, 6 g of a condensation product of higher molecular weight fatty acids and protein degradation products and contains 12 cc sodium hydroxide solution of 38'B6. Then it is adjusted to 3 l with water.

Then the goods are spun and cold in the following hour Bath developed: 6.3 g of 3-amino-2-methyl-4'-methoxy-1,1'-azobenzene are 11.4 ccm hydrochloric acid at 20 ° B6 and 2.3 g sodium nitrite, dissolved in 13 ccm water, diazotized and stirred in a bath containing 3 g of an action product of about 20 moles of ethylene oxide to 1 mole of a fatty alcohol, 30 cc of acetic acid and 9 g of sodium acetate. then is adjusted to 3 l with water.

Then it is acidified with 3 cc hydrochloric acid of 20 ° B6 per liter of water, rinsed well, first treated for 15 minutes at 60 ° C and then 15 minutes at 95 ° C with 5 g of soap and 3 cc of concentrated ammonia per liter of water, rinsed with some formic acid acidified, rinsed and dried.

A full, yellowish red is obtained. Example 11 13 g of 3-amino-6,4'-dimethoxy-1,1'-azobenzene are diazotized in the usual way. The diazo solution thus obtained is left in stir well into a solution of 14 g of 2,3-oxynaphthoylaminobenzene in 300 ccm of 5N sodium hydroxide solution and 150 cc of methyl alcohol. After the coupling is completed, the resulting Dye sucked off, washed out and dried. It's a brownish-purple powder.

The coupling can also be carried out in the presence of a paint preparation suitable carrier.

The following table also contains a number of further components which can be used according to the invention and the color shades of the azo dyes obtainable therefrom on the fiber, which likewise have good fastness properties. Diazo component Azo component Dyed material hue 3-Amino-2-methyl-4'-methoxy-2,3-oxynaphthoylaminobenzene cotton scarlet 1,1'-azobenzene the same. 1- (2 ', 3'-oxynaphthoylamino) - the same. the same. 2-methoxybenzene like. like. like. like. the same. 1- (2 ', 3'-oxynaphthoylamino) - the same. covered 2,5-dimethoxy-4-chlorobenzene scarlet fever likewise 1- (2 ', 3'-oxynaphthoylamino) - likewise scarlet fever 2,3-dimethylbenzene 3-Amino-6-ethoxy-4'-methoxy-1- (2 ', 3'-oxynaphthoylamino) - like garnet 1,1'-azobenzene (F. 67 to 2,4-dimethoxy-5-chlorobenzene 68 ° C) the same. 1- (2 ', 3'-oxynaphthoylamino) - the same. the same. 4-ethoxybenzene also 1- (2 ', 3'-oxynaphthoylamino) - the same yellowish garnet 2-methoxy-4-chloro-5-methyl- benzene likewise 1- (2 ', 3'-oxynaphthoylamino) - the same desgL 2-methoxy-5-chlorobenzene likewise 1- (2 ', 3'-oxynaphthoylamino) - likewise garnet 2,5-dimethoxybenzene 3-Amino-4-ethoxy-4'-methoxy-1- (2 ', 3'-oxynaphthoylamino) - like Bordo 1,1'-azobenzene (F. 159 bis naphthalene 160 ° C) the same. 1- (2 ', 3'-oxynaphthoylamino) - the same. the same. 2-methyl 4-chlorobenzene also 1- (3'-Oxydiphenylenoxyd- like black-brown 2'-carboylamino) naphthalene also 2- (2 ', 3'-oxynaphthoylamino) - the same Bordo naphthalene the same. 1- (2 ', 3'-oxynaphthoylamino) - the same. the same. 4-methylbenzene 3-Amino-6,4'-dimethoxy 1,1'- 1- (2 ', 3'-oxynaphthoylamino) - like bluish garnet azobenzene (m.p. 76 to 77 ° C) 4-methoxybenzene the same. 1- (2 ', 3'-oxynaphthoylamino) - the same. the same. 2-methyl-4-methoxybenzene the same. 1- (2 ', 3'-oxynaphthoylamino) - similarly bluish 3-nitrobenzene garnet likewise 1- (2 ', 3'-oxynaphthoylamino) - likewise bluish garnet 2-methoxy-4-chloro-5-methyl- benzene also 1- (5'-Oxy-1 ', 1 ", 2', 2" -benzo- like black carbazole-4'-carboylamino) - 4-methoxybenzene also 1- (3'-Oxydiphenylenoxyd- like yellowish brown 2'-carboylamino) -2-ethoxy- benzene 3-Amino-4,4'-dimethoxy-1- (2 ', 3'-Oxynaphthoylamino) - the same yellowish red 5-methyl-1,1'-azobenzene 4-chlorobenzene (F. 82 to 83'C) likewise 1- (2'-oxycarbazole-3'-carboyl- similarly yellowish amino) -4-chlorobenzene brown also 1- (3'-Oxydiphenylenoxyd- like black-brown 2'-carboylamino) -2,5-dimeth- oxybenzene likewise 1- (2 ', 3'-oxynaphthoylamino) - likewise scarlet fever 2-ethoxybenzene also 2- (2 ', 3'-oxynaphthoylamino) - the same yellowish red 3-methoxydiphenylene oxide Diazo component Azo component Dye material Color shade - 3-Amino-4,4'-dimethoxy-2-acetoacetylamino-6-ethoxy cotton yellow 5-methyl-1,1'-azobenzene benzthiazole (F. 82 to 83 ° C) 3-Amino-4-methyl-5,6-dichloro-1- (6'-bromo-2 ', 3'-oxynaphthoyl- like red 4'-methoxy-1,1'-azobenzene amino) -2-methoxybenzene (F. 138 to 140 ° C) 3-Amino-4-chloro-4'-methoxy-1- (2 ', 3'-Oxynaphthoylamino) - the same yellowish red 1,1'-azobenzene (F. 113 to 2-methyl-5-chlorobenzene _ 114 ° C) 3-Amino-6-chloro-4'-methoxy-1- (2 ', 3'-Oxynaphthoylamino) - the same yellowish red 1,1'-azobenzene (m.p. 88 to 90 ° C) 2-methyl-4-chlorobenzene The same 4,4'-bisacetoacetylamino-similarly red sticky yellow 3,3'-dimethyldiphenyl 3-Amino-4,6-dimethyl-4'-meth-2,3-oxynaphthoylaminobenzene like Bordo oxy-1,1'-azobenzene (F. 137 bis 138 ° C) Terephthaloylbis-1-acetylamino-similarly red-sticky yellow 2,4-dimethoxy-5-chlorobenzene desgl. Terephthaloylbis-l-acetylan-ino- desgl. desgl. 2-methoxy-4-chloro-5-methyl- benzene likewise 1- (2 ', 3'-oxynaphthoylamino) - likewise bluish red 2,4-dimethylbenzene 3-Amino-4,3-dichloro-4'-methoxy-1- (2 ', 3'-oxynaphthoylamino) - also rust red 1; 1'-azobenzene (F. 148 to 2,5-dimethoxy-4-chlorobenzene 150 ° C) 3-Amino-4-methyl-6-chloro-1- (2 ', 3'-Oxynaphthoylamino) - the same yellowish red 4'-methoxy-1,1'-azobenzene 2,4-dimethoxy-5-chlorobenzene (F. 130 to 132 ° C) 3-Amino-4'-methoxy-1,1'-azo- 1- (2 ', 3'-Oxynaphthoylamino) - the same yellowish - benzene 2,3-dimethylbenzene scarlet 3-Amino-3'-chloro-4'-methoxy-1- (2 ', 3'-oxynaphthoylamino) - the same yellowish 1,1'-azobenzene 2-methoxybenzene scarlet 3-Amino-2'-methyl-4'-methoxy-2,3-oxynaphthoylaminobenzene like rust red 1,1'-azobenzene 3-Amino-3'-methyl-4'-methoxy- like. Like. Scarlet fever 1,1'-azobenzene (F. 88 to 89'C) 3 = Amino-2'-chloro-4'-methoxy-1- (2 ', 3'-oxynaphthoylamino) - the same yellowish tinge 1,1'-azobenzene 2,4-dimethoxy-5-chlorobenzene scarlet 3-Amino-4-methyl-4'-methoxy-1- (2 ', 3'-oxynaphthoylamino) - likewise scarlet fever 1,1'-azobenzene, 2-methoxy-5-chlorobenzene 3-Amino-6-methyl-4'-methoxy-1- (2 ', 3'-oxynaphthoylamino) - also rust red 1,1'-azobenzene 2,5-dimethoxy-4-chlorobenzene 3-Amino-4,4 ', 6-trimethoxy-1- (2', 3'-Oxynaphthoylamino) - like Corinth 1,1'-azobenzene 2,4-dimethoxy-5-chlorobenzene 3-Amino-3 ', 4'-dimethoxy-2,3-oxynaphthoylaminobenzene like - yellowish 1,1'-azobenzene scarlet fever 3-Amino-4'-methoxy- 1- (2 ', 3'-Oxynaphthoylamino) - polyethylene glycol- yellow sticky 1,1'-azobenzene 2-methyl-4-methoxybenzene terephthalate fiber scarlet also 1- (2 ', 3'-oxynaphthoylamino) - the same red-orange 2-methoxybenzene also 1- (2'-oxycarbazole-3'-carboyl- like yellow sticky amino) -2-methoxybenzene brown also 1- (5 ', 6', 7 ', 8'-Tetrahydro- like leather brown 2 ', 3'-oxynaphthoylamino) - naphthalene 3-Amino-4-methyl-4'-methoxy-1- (2 ', 3'-Oxynaphthoylamino) - the same yellowish red 1,1'-azobenzene 2-methyl-4-methoxybenzene also 1- (2 ', 3'-oxynaphthoylamino) - the same yellow sticky 2-methoxybenzene scarlet fever Diazo component Azo component dyed goods hue 3-Amino-4-methyl-4'-meth- 1-acetoacetylamino-2,5-dimeth- polyethylene glycol- yellow - oxy-1,1'-azobenzene oxy-4-chlorobenzene terephthalate fiber the same. 4,4'-bisacetoacetylamino- like. like. 3,3'-dimethyldiphenyl 3-Amino-6-chloro-4'-methoxy-1- (2 ', 3'-Oxynaphthoylamino) - the same yellowish 1,1'-azobenzene 2-methyl-4-methoxybenzene scarlet also 1- (2 ', 3'-oxynaphthoylamino) - the same red-orange 2-methoxybenzene likewise 1- (2'-oxycarbazole-3'-carboyl- similarly yellowish amino) -2-methoxybenzene brown desgl- 1-acetoacetylamino-2,5-dimeth- like yellow oxy-4-chlorobenzene 3-Amino-4'-methoxy-1,1'-azo-4,4'-bisacetoacetylamino like the like. benzene 3,3'-dimethyldiphenyl the same. 2-Acetoacetylamino-6-ethoxy- desgl- desgl. benzthiazole 3-Amino-4,4'-dimethoxy-1- (2 ', 3'-Oxynaphthoylamino) - also bluish red 1,1'-azobenzene 2-methoxybenzene also 1- (2'-oxycarbazole-3'-carboyl- like red-brown amino) -2-methoxybenzene like 1- (5 ', 6', 7 ';8'-tetrahydro- like. 2 ', 3'-oxynaphthoylamino) - naphthalene 1-acetoacetylamino-2,5-dimeth- like old gold oxy-4-chlorobenzene 4,4'-bisacetoacetylamino like yellow 3,3'-dimethyldiphenyl 3-Amino-4-methyl-6-chloro-1- (2 ', 3'-oxynaphthoylamino) - like scarlet fever 4'-methoxy-1,1'-azobenzene 2-methoxybenzene 3-Amino-4'-ethoxy-1,1'-azo-like. Like. Red-orange benzene 3-Amino-4'-methoxy-1,1'-azo-1-benzoylacetylamino-2,5-di- like golden yellow benzene methoxy-4-benzoylamino- benzene 3-Amino-4-ethoxy-4'-methoxy-1- (2'-oxyanthracene-3'-carboyl-cotton Corinth 1,1'-azobenzene amino) -2-methylbenzene

Claims (1)

PATENT CLAIM: Process for the preparation of water-insoluble azo dyes, characterized in that the diazonium compounds are obtained from m-aminoazo compounds of the general formula wherein the benzene nuclei .a and b can be substituted by halogen atoms, alkyl, alkoxy or nitro groups, with arylamides of aromatic or heterocyclic o-oxycarboxylic acids or of acyl acetic acids which are free of water-solubilizing groups, in substance, on the fiber or on one other substrate couples. Considered publications: German patent specification No. 609 334. When the application was published, two coloring tables with explanations were laid out.